Discussed with the exchange team yesterday and they can’t see issues. For any email that does not get send does not seem to actually reach the exchange server. I asked them to look more thoroughly as this seemed very odd but logs they showed me only had emails that actually did come through.
As I’m pretty desperate with this I actually setup a new server for this where I migrated our DB. Original setup was on RedHat 8.7 with Passbolt version 3.8.0 - new one is on Ubuntu 22.04 with Passbolt 4.0.2. Sadly the same issue persists although I’m quite liking the few new features that have come along since our initial install!
One of my team members had an issue after install where his browser was just taking him to the registration page instead of logon. He noticed that when he did the registration twice in quick succession the email actually came through. I can see that on the email_queue table on the DB too that the first one failed and second one worked. This also seemingly followed the “every other email works” pattern we saw. Still don’t know if this is coincidence or not but it seems to have too much repetition to be totally random occurrence.
Below sample from the table - the cases where the “every other” pattern breaks so that there are multiple emails that fail to send 4 times in a row are all 100% cases where registration/recovery has been tried. Maybe this is one form of workaround we have now that we just spam the registration/recovery until an email comes through but seems very sad for a SW that works so well otherwise. Its also annoying that someone always misses the “edit” notifications.
mysql> SELECT email, sent, send_tries, send_at, created, error FROM email_queue ORDER BY id DESC LIMIT 40;
+----------------------------+------+------------+---------------------+---------------------+----------------------------------------------------------------------------+
| email | sent | send_tries | send_at | created | error |
+----------------------------+------+------------+---------------------+---------------------+----------------------------------------------------------------------------+
| obscured@passbolt.com | 1 | 0 | 2023-05-30 12:06:47 | 2023-05-30 12:06:47 | NULL |
| obscured@passbolt.com | 0 | 4 | 2023-05-30 12:05:41 | 2023-05-30 12:05:41 | SMTP authentication method not allowed, check if SMTP server requires TLS. |
| obscured@passbolt.com | 1 | 0 | 2023-05-30 11:50:32 | 2023-05-30 11:50:32 | NULL |
| obscured@passbolt.com | 0 | 4 | 2023-05-30 11:48:10 | 2023-05-30 11:48:10 | SMTP authentication method not allowed, check if SMTP server requires TLS. |
| obscured@passbolt.com | 0 | 4 | 2023-05-30 11:42:24 | 2023-05-30 11:42:24 | SMTP authentication method not allowed, check if SMTP server requires TLS. |
| obscured@passbolt.com | 1 | 0 | 2023-05-29 11:42:50 | 2023-05-29 11:42:50 | NULL |
| obscured@passbolt.com | 1 | 1 | 2023-05-29 11:42:50 | 2023-05-29 11:42:50 | SMTP authentication method not allowed, check if SMTP server requires TLS. |
| obscured@passbolt.com | 1 | 0 | 2023-05-29 11:42:50 | 2023-05-29 11:42:50 | NULL |
| obscured@passbolt.com | 1 | 2 | 2023-05-29 11:42:50 | 2023-05-29 11:42:50 | SMTP authentication method not allowed, check if SMTP server requires TLS. |
| obscured@passbolt.com | 1 | 0 | 2023-05-29 11:42:42 | 2023-05-29 11:42:42 | NULL |
| obscured@passbolt.com | 1 | 1 | 2023-05-29 11:42:42 | 2023-05-29 11:42:42 | SMTP authentication method not allowed, check if SMTP server requires TLS. |
| obscured@passbolt.com | 1 | 0 | 2023-05-29 11:42:42 | 2023-05-29 11:42:42 | NULL |
| obscured@passbolt.com | 0 | 4 | 2023-05-29 11:42:42 | 2023-05-29 11:42:42 | SMTP authentication method not allowed, check if SMTP server requires TLS. |
| obscured@passbolt.com | 1 | 0 | 2023-05-29 11:42:29 | 2023-05-29 11:42:29 | NULL |
| obscured@passbolt.com | 1 | 1 | 2023-05-29 11:42:29 | 2023-05-29 11:42:29 | SMTP authentication method not allowed, check if SMTP server requires TLS. |
| obscured@passbolt.com | 1 | 0 | 2023-05-29 11:42:29 | 2023-05-29 11:42:29 | NULL |
| obscured@passbolt.com | 1 | 2 | 2023-05-29 11:42:29 | 2023-05-29 11:42:29 | SMTP authentication method not allowed, check if SMTP server requires TLS. |
| obscured@passbolt.com | 1 | 0 | 2023-05-29 11:42:22 | 2023-05-29 11:42:22 | NULL |
| obscured@passbolt.com | 1 | 2 | 2023-05-29 11:41:58 | 2023-05-29 11:41:58 | SMTP authentication method not allowed, check if SMTP server requires TLS. |
| obscured@passbolt.com | 1 | 0 | 2023-05-29 11:41:58 | 2023-05-29 11:41:58 | NULL |
| obscured@passbolt.com | 1 | 1 | 2023-05-29 11:41:58 | 2023-05-29 11:41:58 | SMTP authentication method not allowed, check if SMTP server requires TLS. |
| obscured@passbolt.com | 1 | 0 | 2023-05-29 11:41:58 | 2023-05-29 11:41:58 | NULL |
| obscured@passbolt.com | 0 | 4 | 2023-05-29 11:41:49 | 2023-05-29 11:41:49 | SMTP authentication method not allowed, check if SMTP server requires TLS. |
| obscured@passbolt.com | 0 | 4 | 2023-05-29 11:12:09 | 2023-05-29 11:12:09 | SMTP authentication method not allowed, check if SMTP server requires TLS. |
| obscured@passbolt.com | 0 | 4 | 2023-05-29 11:08:24 | 2023-05-29 11:08:24 | SMTP authentication method not allowed, check if SMTP server requires TLS. |
| obscured@passbolt.com | 1 | 2 | 2023-05-29 09:38:56 | 2023-05-29 09:38:56 | SMTP authentication method not allowed, check if SMTP server requires TLS. |
| obscured@passbolt.com | 1 | 0 | 2023-05-29 09:38:56 | 2023-05-29 09:38:56 | NULL |
| obscured@passbolt.com | 1 | 1 | 2023-05-29 09:38:56 | 2023-05-29 09:38:56 | SMTP authentication method not allowed, check if SMTP server requires TLS. |
| obscured@passbolt.com | 1 | 0 | 2023-05-29 09:38:56 | 2023-05-29 09:38:56 | NULL |
| obscured@passbolt.com | 0 | 4 | 2023-05-29 09:38:47 | 2023-05-29 09:38:47 | SMTP authentication method not allowed, check if SMTP server requires TLS. |
| obscured@passbolt.com | 1 | 0 | 2023-05-29 08:54:40 | 2023-05-29 08:54:40 | NULL |
| obscured@passbolt.com | 0 | 4 | 2023-05-29 08:54:40 | 2023-05-29 08:54:40 | SMTP authentication method not allowed, check if SMTP server requires TLS. |
| obscured@passbolt.com | 1 | 0 | 2023-05-29 08:54:40 | 2023-05-29 08:54:40 | NULL |
| obscured@passbolt.com | 1 | 1 | 2023-05-29 08:54:40 | 2023-05-29 08:54:40 | SMTP authentication method not allowed, check if SMTP server requires TLS. |
| obscured@passbolt.com | 1 | 0 | 2023-05-29 08:54:23 | 2023-05-29 08:54:23 | NULL |
| obscured@passbolt.com | 1 | 0 | 2023-05-29 08:53:56 | 2023-05-29 08:53:56 | NULL |
| obscured@passbolt.com | 1 | 3 | 2023-05-29 08:53:56 | 2023-05-29 08:53:56 | SMTP authentication method not allowed, check if SMTP server requires TLS. |
| obscured@passbolt.com | 1 | 0 | 2023-05-29 08:53:56 | 2023-05-29 08:53:56 | NULL |
| obscured@passbolt.com | 1 | 1 | 2023-05-29 08:53:56 | 2023-05-29 08:53:56 | SMTP authentication method not allowed, check if SMTP server requires TLS. |
| obscured@passbolt.com | 1 | 0 | 2023-05-29 08:53:44 | 2023-05-29 08:53:44 | NULL |
+----------------------------+------+------------+---------------------+---------------------+----------------------------------------------------------------------------+
40 rows in set (0.00 sec)